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Updated:
Hey folks, we have made some improvements to our shuffle algorithm that we are turning on as a default for all users. We'd love your feedback on how your shuffle experience changes after today (Feb 5, 2016). Thanks for your feedback, your comments are essential to helping us improve Spotify.
Update Aug 2018:
Hi folks, it sounds like quite a few of you are experiencing only the top tracks in a playlist shuffling/ playing when using Connect. This has already been reported here.
We’ve given a transparent status there explaining there isn’t a current timeline for a fix. Please do leave a VOTE there if you’re experiencing the issue and a comment. We can then bring this information back internally to show the size of the issue for our users.
If however you are experiencing issues with Shuffle when not using Connect, please get back to us in this thread we've the questions we've listed and click +VOTE. Thank you!